Dichloromethane → HCID 178445723, compound

HRID 1036478Notes

Reaction equation

HRID 1036478 reaction equation
Br[C:2]1[C:11]([O:12][CH:13]2[CH2:18][CH2:17][CH:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C@:23]1([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]1)=[CH:7]2.ClCCl.C(=O)([O-])[O-].[Cs+].[Cs+].O1[CH2:43][CH2:42][CH2:41]C1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:19]([C@H:16]1[CH2:17][CH2:18][C@H:13]([O:12][C:11]2[C:2]([CH:41]3[CH2:42][CH2:43]3)=[C:3]3[C:8](=[CH:9][CH:10]=2)[CH:7]=[C:6]([C@:23]2([CH3:29])[CH2:27][O:26][C:25](=[O:28])[NH:24]2)[CH:5]=[CH:4]3)[CH2:14][CH2:15]1)([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 67413119(R)-4-(5-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 178445723HCID 178445723, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×

Procedure

(R)-4-[5-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.2047 g, 0.0004446 mol), cyclopropyl trifluoroborate potassium salt (0.0658 g, 0.000445 mol), [1,1′Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.03 g, 0.00004 mol) and cesium carbonate (0.434 g, 0.00133 mol) were added to a capped 40 mL vial equipped with a magnetic stir bar. The vial was degassed and purged with nitrogen. tetrahydrofuran (5.00 mL, 0.0616 mol) and water (0.50 mL, 0.028 mol) were added and the reaction mixture was stirred at reflux for 24 h under a nitrogen atmosphere. HPLC analysis showed that the reaction was complete. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethylacetate. The combined organic extracts were washed with 1N HCl (20 mL) and brine (20 mL) and then dried over magnesium sulfate. The solvent was removed under vacuum and the crude product was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give 109.3 mg of the title compound (58% yield).

Workup

  1. customvial equipped with a magnetic stir bar
  2. customThe vial was degassed
  3. custompurged with nitrogen
  4. temperatureat reflux for 24 h under a nitrogen atmosphere
  5. extractionextracted with ethylacetate
  6. washThe combined organic extracts were washed with 1N HCl (20 mL) and brine (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under vacuum
  9. customthe crude product was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e711973c5d04979a4ecc8da56da569d
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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